IP Library Granted Patent US 8,945,338
Granted Patent B2
US 8,945,338 · App. 13/839,785 · Granted Feb 3, 2015

Anaerobic curable compositions

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,945,338
App. No.
13/839,785
Granted
Feb 3, 2015
Kind
B2
Abstract

The invention provides anaerobic curable compositions, and methods of their production and use. These compositions provide excellent adhesion especially on oily surfaces.

Claims (41)

1. An anaerobically curable composition comprising:

at least one (meth)acrylate component;

an anaerobic cure system; and

a biodegradable oleaginous plasticizer.

2. The composition of claim 1 , wherein the biodegradable oleaginous plasticizer comprises a soybean oil component.

3. The composition of claim 1 , wherein the biodegradable oleaginous plasticizer is an alkyl ester of soybean oil.

4. The composition of claim 1 , wherein the (meth)acrylate component is represented by H 2 C═C(G)CO 2 R 1 , wherein G is a member selected from the group consisting of H, halogen and alkyl having from 1 to about four carbon atoms, and R 1 is a member selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, and aryl groups having from 1 to about 16 carbon atoms, with or without substitution or interruption by a member selected from the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbamate, amine, amide, sulfur, sulfonate and sulfone.

5. The composition according to claim 1 , wherein the (meth)acrylate component is a member selected from the group consisting of silicone (meth)acrylates, polyethylene glycol di(meth)acrylates, bisphenol-A-(meth)acrylates, ethoxylated bisphenol-A-(meth)acrylates, bisphenol-F-(meth)acrylates, ethoxylated bisphenol-F-(meth)acrylates, tetrahydrofuran(meth)acrylates and di(meth)acrylates, hydroxypropyl(meth)acrylate, hexanediol di(meth)acrylate, and trimethylol propane tri(meth)acrylate.

6. The composition of claim 1 , wherein the biodegradable oleaginous plasticizer is present in an amount of about 1.0 percent to about 40.0 percent by weight of the total composition.

7. The composition of claim 1 , wherein the (meth)acrylate component is present in an amount of about 50 percent to about 90 percent by weight of the total composition.

8. The composition of claim 1 , further comprising a material selected from the group consisting of thickeners, coloring agents, chelators, diluents and combinations thereof.

9. An anaerobic composition comprising:

a (meth)acrylate component in the amount of about 50 percent to about 90 percent by weight of the total composition;

an anaerobic cure system; and

a biodegradable oleaginous plasticizer in an amount of about 1.0 percent to about 40.0 percent by weight of the total composition.

10. The composition of claim 9 , wherein the anaerobic cure system comprises a cure initiator in the amount of 0.1 percent to about 5 percent by weight of the total composition and a cure accelerator in the amount of about 0.1 percent to about 5 percent by weight of the total composition.

11. The composition of claim 9 , wherein the biodegradable oleaginous plasticizer comprises an alkyl ester of soybean oil.

12. The composition of claim 9 , wherein the biodegradable oleaginous plasticizer is a methyl ester of soybean oil.

13. The composition of claim 12 , wherein the methyl ester of soybean oil is present in an amount of about 1 percent to about 15 percent by weight of the total composition.

14. The composition of claim 1 , wherein the break strength of the cured composition after 24 hours on oily nut/bolt assembly is about 80 to about 180 inch-pounds.

15. The composition of claim 1 , wherein the prevail strength of the cured composition after 24 hours on an oily nut/bolt assembly is about 25 to about 80 inch-pounds.

16. The composition of claim 9 , further comprising a material selected from the group consisting of thickeners, coloring agents, chelators, diluents and combinations thereof.

17. A method of preparing an adhesive composition comprising:

forming a composition comprising at least one (meth)acrylate component and a cure system; and

combining said composition with a biodegradable oleaginous plasticizer in an amount of 1.0 percent to about 40.0 percent by weight of the total composition.

18. The method of claim 17 , wherein said biodegradable oleaginous plasticizer is an alkyl ester of soybean oil.

19. A method of bonding oily surfaces comprising the steps of:

providing an adhesive composition comprising;

at least one (meth)acrylate component;

a cure system; and

a biodegradable oleaginous plasticizer;

applying said composition to an oily surface of a substrate;

mating said substrate with another substrate; and

permitting said composition to cure.

20. The method of claim 19 , wherein the oily substrate surface is constructed from a material selected from zinc, steel, stainless steel, cadmium and combinations thereof.

21. The method of claim 19 , wherein the oily substrate is a nut or bolt.

22. A method for using an anaerobically curable composition, said method comprising the steps of:

(a) providing an anaerobically curable composition in accordance with claim 1 ;

(b) providing two or more substrates, each of which having at least one complimentary surface;

(c) applying said anaerobically curable composition to at least one of said complimentary surfaces of the substrates; and

(d) mating said complimentary surfaces of the substrates such that said anaerobically curable composition is disposed therebetween in an anaerobic environment and permitting said anaerobically curable composition to cure.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2015
From: HENKEL CORPORATION
To: HENKEL US IP LLC
Reel/Frame 035049/0904 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2015
From: HENKEL US IP LLC
To: HENKEL IP & HOLDING GMBH
Reel/Frame 035050/0378 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2015
From: HENKEL US IP LLC
To: HENKEL IP & HOLDING GMBH
Reel/Frame 035101/0856 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2015
From: MESSANA, ANDREW D.; HURLBURT, LYNNETTE; SCHALL, JOEL D.
To: HENKEL CORPORATION
Reel/Frame 034808/0821 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2014
From: HENKEL CORPORATION
To: HENKEL US IP LLC
Reel/Frame 034186/0588 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2014
From: LIU, JIANPING; MAANDI, ANDRUS
To: HENKEL CORPORATION
Reel/Frame 032298/0594 →